Details of the Drug

General Information of Drug (ID: DM7R3B6)

Drug Name

Nobiletin

Synonyms

478-01-3; Hexamethoxyflavone; 3',4',5,6,7,8-Hexamethoxyflavone; 5,6,7,8,3',4'-Hexamethoxyflavone; UNII-D65ILJ7WLY; 2-(3,4-Dimethoxyphenyl)-5,6,7,8-tetramethoxy-4H-1-benzopyran-4-one; 2-(3,4-dimethoxyphenyl)-5,6,7,8-tetramethoxychromen-4-one; NSC-76751; D65ILJ7WLY; 2-(3,4-dimethoxyphenyl)-5,6,7,8-tetramethoxy-4H-chromen-4-one; CHEMBL76447; Nobiletin (Hexamethoxyflavone); CHEBI:7602; NSC76751; MFCD03273560; Flavone, 5,6,7,8,3',4'-hexamethoxy; 4H-1-Benzopyran-4-one, 2-(3,4-dimethoxyphenyl)-5,6,7,8-tetramethoxy-; SMR000156231; CCRIS 9012; NSC 76751; CPD000156231; Nobiletin, >=97%; Spectrum2_001697; Spectrum3_000921; Spectrum4_001020; KBioGR_001519; MLS000574877; MLS000759462; MLS000877030; MLS001424129; Nobiletin, analytical standard; SCHEMBL244029; SPECTRUM1505268; SPBio_001654; MEGxp0_000930; ACon1_000921; KBio3_001922; DTXSID30197275; 2-(3,4-dimethoxyphenyl)-5,6,7,8-tetramethoxy-chromen-4-one; HMS2051D09; HMS2234A09; HMS3373C14; HMS3393D09; HMS3651G20; HY-N0155; ZINC1531669; 3'4'5,6,7,8-Hexamethoxyflavone; 3,4,5,6,7,8-Hexamethoxyflavone; ANW-42631; BDBM50338976; CCG-38781; CN0043; LMPK12111468; NSC618903; STL565829; AKOS015965334; NOBILETIN, 20% (Technical Grade); AC-1023; CS-5518; MCULE-1015144950; NC00186; NSC-618903; SDCCGMLS-0066776.P001; NCGC00095703-01; NCGC00095703-02; NCGC00169228-01; 5,6,7,8,3'',4''-hexamethoxyflavone; AK168175; AS-17452; NCI60_041691; DB-050181; FT-0686667; N0871; N1311; S2333; SW197566-2; V0181; C10112; SR-01000712262; Q-100511; Q2402963; SR-01000712262-5; BRD-K06753942-001-02-0; 2-(3,4-Dimethoxy-phenyl)-5,6,7,8-tetramethoxy-chromen-4-one; 4H-1-Benzopyran-4-one,4-dimethoxyphenyl)-5,6,7,8-tetramethoxy-; 2-(3,4-Dimethoxyphenyl)-5,6,7,8-tetramethoxy-4H-1-benzopyran-4-one, 9CI; 3 inverted exclamation mark ,4 inverted exclamation mark ,5,6,7,8-HEXAMETHOXYFLAVONE; 4H-1-Benzopyran-4-one, 2-(3,4-dimethoxyphenyl)-5,6,7,8-tetramethoxy- (9CI)

Indication

Disease Entry	ICD 11	Status	REF
Atherosclerosis	BD40	Preclinical	[1]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

402.4

Logarithm of the Partition Coefficient (xlogp)

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

Chemical Identifiers

Formula: C21H22O8
IUPAC Name: 2-(3,4-dimethoxyphenyl)-5,6,7,8-tetramethoxychromen-4-one
Canonical SMILES: COC1=C(C=C(C=C1)C2=CC(=O)C3=C(O2)C(=C(C(=C3OC)OC)OC)OC)OC
InChI: InChI=1S/C21H22O8/c1-23-13-8-7-11(9-15(13)24-2)14-10-12(22)16-17(25-3)19(26-4)21(28-6)20(27-5)18(16)29-14/h7-10H,1-6H3
InChIKey: MRIAQLRQZPPODS-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 72344
ChEBI ID: CHEBI:7602
CAS Number: 478-01-3
TTD ID: D4PG6A

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Nuclear receptor ROR-gamma (RORG)	TTGV6LY	RORG_HUMAN	Agonist	[2]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Asparagine synthetase (ASNS)	OT8R922G	ASNS_HUMAN	Gene/Protein Processing	[3]
Caspase-8 (CASP8)	OTA8TVI8	CASP8_HUMAN	Protein Interaction/Cellular Processes	[4]
Cyclin-A2 (CCNA2)	OTPHHYZJ	CCNA2_HUMAN	Gene/Protein Processing	[3]
Cytochrome P450 1A1 (CYP1A1)	OTE4EFH8	CP1A1_HUMAN	Regulation of Drug Effects	[5]
Cytochrome P450 1A2 (CYP1A2)	OTLLBX48	CP1A2_HUMAN	Regulation of Drug Effects	[5]
Cytochrome P450 1B1 (CYP1B1)	OTYXFLSD	CP1B1_HUMAN	Gene/Protein Processing	[5]
Cytochrome P450 3A4 (CYP3A4)	OTQGYY83	CP3A4_HUMAN	Gene/Protein Processing	[6]
DEP domain-containing protein 1A (DEPDC1)	OT0JWE1B	DEP1A_HUMAN	Gene/Protein Processing	[3]
DNA damage-inducible transcript 3 protein (DDIT3)	OTI8YKKE	DDIT3_HUMAN	Gene/Protein Processing	[3]
G1/S-specific cyclin-E2 (CCNE2)	OTBBUKQQ	CCNE2_HUMAN	Gene/Protein Processing	[3]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	Circadian rhythm as a therapeutic target. Nat Rev Drug Discov. 2021 Apr;20(4):287-307.
2	The Small Molecule Nobiletin Targets the Molecular Oscillator to Enhance Circadian Rhythms and Protect against Metabolic Syndrome. Cell Metab. 2016 Apr 12;23(4):610-21.
3	Characteristics of nobiletin-mediated alteration of gene expression in cultured cell lines. Biochem Biophys Res Commun. 2013 Feb 15;431(3):530-4.
4	Polymethoxyflavones from citrus inhibited gastric cancer cell proliferation through inducing apoptosis by upregulating RAR, both in vitro and in vivo. Food Chem Toxicol. 2020 Dec;146:111811. doi: 10.1016/j.fct.2020.111811. Epub 2020 Oct 12.
5	Bioactivation of the citrus flavonoid nobiletin by CYP1 enzymes in MCF7 breast adenocarcinoma cells. Food Chem Toxicol. 2012 Sep;50(9):3320-8.
6	Heterotropic activation of flavonoids on cytochrome P450 3A4: A case example of alleviating dronedarone-induced cytotoxicity. Toxicol Lett. 2020 Feb 1;319:187-196. doi: 10.1016/j.toxlet.2019.11.016. Epub 2019 Nov 19.